There’s probably no such thing as a good cop, bad cop, middle cop. But for Justin Hartzman, it seems necessary to tweak the trope in order to describe his lifelong friendship with Jeremy Koven and Michael Koral.

“We all balance each other out… we play to each other’s strengths,” explains the entrepreneur. “We got into (business together) knowing it so we know what to expect from the other person.”

For a decade and a half, the trio has been building businesses together, but they’ve known each other since they were kids.

“We’ve had three exits, two in one year, 2005, back-to-back, then one about two and a half years ago,” says Hartzman. “Now we run two startups in the city.”

Those startups are CoinSmart, one of the largest cryptocurrency exchanges in Canada, and Needls, the internet’s first Robo ad agency which uses AI for automated social media advertising at a price that fits within small and medium-sized business’ budgets.

The startups seem to hover in completely different universes, but that’s always been their m.o. They’ve tackled everything from skins and resources for customizing MySpace pages, website brokering, and AllYouCanEatInternet, a consultancy set up to help companies create and market businesses. But there’s an underlying method, promises Hartzman.

“What we’re always looking for whenever we move into anything is who is the most underserved market and how can we do the best job to serve those people who have never been served before?” says Hartzman. “Is that succinct enough?”

Hartzman calls himself the “aggressive and loud” one of the trio. “Michael is the exact opposite – calm, relaxed, focused and Jeremy is somewhere in the middle.”

But despite their tightly-knit approach, building multiple businesses in Toronto means the entrepreneurs have watched the ecosystem here crawl forward from infancy.

“Toronto is now coming into its own, it’s taken a really long time, as someone who’s been in the space awhile,” he says. “It was very tough to be a startup in our city up until three or four years ago where there was a dynamic shift.”

Hartzman says two years ago, if someone came to him for advice on raising funding in the city, he’d be likely to tell them to look outside the city (he says he raised most of his money from the US.) But opinions are changing.

“I’ve never taken the approach of being at the forefront and in people’s faces but I think myself and the colleagues and everyone around me have helped to drive a lot of these pieces from the background, trying to do it ourselves and make something big of it,” says Hartzman. 

Not that he’s dwelling in well-trodden markets. Hartzman and co.’s penchant for underserved markets had led them into the frontiers of advertising tech and cryptocurrency. “We’ve been in the cryptocurrency stage since the start, I think (it’s) where cannabis was five or six years ago,” he says. “We have a lot of learning curve to go, regulation to come and a huge market to tap into in the future… we’re here and ready for it.”

And he’ll do so with his best friends at his side.